Research Progress in Earth-Abundant Metal-Catalyzed Hydroxyazidation of Alkenes

doi:10.6023/cjoc202604006

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (7): 2581-2588.DOI: 10.6023/cjoc202604006 Previous Articles Next Articles

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丰产金属催化烯的羟基叠氮化反应进展

谢东, 韩维^*()

南京师范大学化学与材料科学学院南京 210023

收稿日期:2026-04-02 修回日期:2026-05-14 发布日期:2026-06-10
基金资助:
国家自然科学基金(22371126); 国家自然科学基金(21776139); 江苏省高校基础科学研究(自然科学)重大项目(25KJA150003); 江苏省合成生物学基础研究中心(BK20233003); 江苏省高校“青蓝工程”中青年学术带头人项目; 江苏省自然科学基金(BK20161553); 以及江苏省高校优势学科建设工程资助项目

Research Progress in Earth-Abundant Metal-Catalyzed Hydroxyazidation of Alkenes

Dong Xie, Wei Han^*()

School of Chemistry and Materials Science, Nanjing Normal University, Nanjing 210023

Received:2026-04-02 Revised:2026-05-14 Published:2026-06-10
Contact: *E-mail: whhanwei@outlook.com
Supported by:
National Natural Science Foundation of China(22371126); National Natural Science Foundation of China(21776139); Major Program of Jiangsu Higher Education Institutions for Basic Science (Natural Science)(25KJA150003); Jiangsu Basic Research Center for Synthetic Biology(BK20233003); “Qing Lan Project” Young and Middle-aged Academic Leaders of Jiangsu Provincial Colleges and Universities; Natural Science Foundation of Jiangsu Province(BK20161553); Priority Academic Program Development of Jiangsu Higher Education Institutions

The catalytic hydroxyazidation of alkenes by earth-abundant metal catalysts has garnered significant attention for its efficient and economical construction of β-azido alcohol scaffolds. Recent advances in manganese, copper, cobalt, and iron-based catalytic systems for this transformation are reviewed, covering reaction mechanisms, selectivity control, substrate scope, and synthetic applications, while developmental trends and prospects for earth-abundant metal-catalyzed hydroxyazidation of alkenes are also outlined.

Key words: alkene, earth-abundant metal, bifunctionalization, β-azido alcohol, anti-Markovnikov selectivity

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Dong Xie, Wei Han. Research Progress in Earth-Abundant Metal-Catalyzed Hydroxyazidation of Alkenes[J]. Chinese Journal of Organic Chemistry, 2026, 46(7): 2581-2588.

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Fig. & Tab. 11

Scheme 1. Mn-catalyzed Markovnikov hydroxyazidation of alkenes

Scheme 2. Mn-catalyzed highly efficient aerobic oxidative hydroxyazidation of olefins

Scheme 3. Mechanism of Mn-catalyzed aerobic oxidative hydroxyazidation of olefins

Scheme 4. MnBr2-catalyzed aerobic oxyazidation of fluoroolefins

Scheme 5. Photochemical Mn-mediated hydroxyazidation of alkene

Scheme 6. Copper-catalyzed 1,2-azidooxygenation of 1,3- dienes

Scheme 7. Cobalt-catalyzed regioselective hydroxyazidation of 1,3-dienes

Scheme 8. Dearomatization of indoles via azido radical addition and dioxygen trapping to access 2-azidoindolin-3-ols

Scheme 9. Bioinspired P450 anti-Markovnikov hydroxyazidation of alkenes

Scheme 10. Iron-catalyzed anti-Markovnikov hydroxyazidation of unactivated alkenes

Scheme 11. Proposed mechanism

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丰产金属催化烯的羟基叠氮化反应进展

Research Progress in Earth-Abundant Metal-Catalyzed Hydroxyazidation of Alkenes

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Fig. & Tab. 11

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